tetrahydrobenzo[1,2]indolizino[8,7-b]indole | 65020-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tetrahydrobenzo[1,2]indolizino[8,7-b]indole
• 英文别名: 7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indole；5,7,8,13b-Tetrahydro-13H-indolo<2.3-c>isoindolo<2.1-a>pyridin；14-nor-yohimba-15,17,19-triene；7,8,13,13b-tetrahydro-5H-benz[1,2]indolizino[8,7-b]indole；10,20-diazapentacyclo[11.7.0.02,10.03,8.014,19]icosa-1(13),3,5,7,14,16,18-heptaene
• CAS: 65020-22-6
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: JVHLWTOVJFEQIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tetrahydrobenzo[1,2]indolizino[8,7-b]indole 在 氨 、 sodium 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 20.0h， 生成 10-Methyl-10,20-diazatetracyclo[11.7.0.03,8.014,19]icosa-1(13),3,5,7,14,16,18-heptaene
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 10: SAR Studies on Azecine-type Dopamine Receptor Ligands by Functional Screening at Human Cloned D₁, D_2L, and D₅ Receptors with a Microplate Reader Based Calcium Assay Lead to a Novel Potent D₁/D₅ Selective Antagonist

  摘要：

  On the basis of the benz[d]indolo[2,3-g]azecine derivative I (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D-1, D-2L, and D-5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments. Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead I in the functional calcium assay as well as in radioligand displacement experiments.

  DOI：

  10.1021/jm050846j
• 作为产物：
  描述：

  3-(2-(Isoindolin-2-yl)ethyl)-1H-indole 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以48 mg的产率得到tetrahydrobenzo[1,2]indolizino[8,7-b]indole
  参考文献：
  名称：

  使用异吲哚umpolung一锅法合成多环异吲哚啉

  摘要：

  使用异吲哚umpolung 策略，完成了多环异吲哚啉的一锅法合成。在该反应中，原位产生的亲核异吲哚通过质子化转化为亲电子异吲哚，其经历 Pictet-Spengler 型环化反应，以良好的收率得到多种多环异吲哚啉。

  DOI：

  10.1016/j.tetlet.2020.152128

文献信息

• Synthesis of azecino[5,4-b]indoles and indolo[3,2-e][2]benzazonines via tandem transformation of hydrogenated indoloquinolizines and indolizines
  作者：L. G. Voskressensky、T. N. Borisova、A. A. Titov、A. V. Listratova、L. N. Kulikova、A. V. Varlamov、V. N. Khrustalev、G. G. Aleksandrov

  DOI：10.1007/s11172-012-0167-6

  日期：2012.6

  The reactions of partially hydrogenated indole-fused quinolizines and indolizines with activated alkynes in methanol, acetonitrile, and dichloromethane were studied. The reactions were shown to be accompanied by the cleavage of the bridging C-N bond. Azecino[5,4-b]-indole and indolo[3,2-e][2]benzazonine derivatives were synthesized.

  研究了部分氢化的吲哚融合喹啉和吲哚啉与活化炔烃在甲醇、乙腈和二氯甲烷中的反应。研究表明，反应伴随着桥接C-N键的断裂。合成了Azecino[5,4-b]-吲哚和indolo[3,2-e][2]苯氮杂烯衍生物。
• POGOSYAN S. A.; TERZYAN A. G.; TATEVOSYAN G. T., AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1977,
  作者：POGOSYAN S. A.、 TERZYAN A. G.、 TATEVOSYAN G. T.

  DOI：——

  日期：——
• Dopamine/Serotonin Receptor Ligands. 10: SAR Studies on Azecine-type Dopamine Receptor Ligands by Functional Screening at Human Cloned D₁, D_2L, and D₅ Receptors with a Microplate Reader Based Calcium Assay Lead to a Novel Potent D₁/D₅ Selective Antagonist
  作者：Barbara Hoefgen、Michael Decker、Patrick Mohr、Astrid M. Schramm、Sherif A. F. Rostom、Hussein El-Subbagh、Peter M. Schweikert、Dirk R. Rudolf、Matthias U. Kassack、Jochen Lehmann

  DOI：10.1021/jm050846j

  日期：2006.1.1

  On the basis of the benz[d]indolo[2,3-g]azecine derivative I (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D-1, D-2L, and D-5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments. Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead I in the functional calcium assay as well as in radioligand displacement experiments.
• One-pot synthesis of polycyclic isoindolines using isoindole umpolung
  作者：Rachel A. Weintraub、Wei He、Xiang Wang

  DOI：10.1016/j.tetlet.2020.152128

  日期：2020.7

  Using an isoindole umpolung strategy, a one-pot synthesis of polycyclic isoindolines was accomplished. In this reaction, the in situ-generated nucleophilic isoindoles were converted to electrophilic isoindoliums via protonation, which underwent a Pictet-Spengler-type cyclization to afford a variety of polycyclic isoindolines in good yields.

  使用异吲哚umpolung 策略，完成了多环异吲哚啉的一锅法合成。在该反应中，原位产生的亲核异吲哚通过质子化转化为亲电子异吲哚，其经历 Pictet-Spengler 型环化反应，以良好的收率得到多种多环异吲哚啉。